New Tax Technology: Avoid These 5 Change Management Pitfalls 

Many tax leaders assume that the most challenging part of adopting new tax technology is securing the budget and implementing it. But that’s just the beginning. Despite the best intentions, research shows that 70% of digital transformation projects fail, with up to 70% of ERP projects missing their objectives, deadlines, or budgets. The problem isn’t usually the technology itself; it’s how organizations handle the human side of change. 

Tax leaders face unique challenges when rolling out new systems. Your teams already juggle complex regulatory requirements, tight compliance deadlines, and the constant pressure of evolving tax laws. Adding technology change management to this mix can push even the most resilient professionals toward burnout and resistance. 

The good news? Most implementation failures stem from predictable pitfalls that you can avoid with the right approach. By understanding where others have stumbled and applying proven change management strategies, you can increase your chances of success while protecting your team’s morale and productivity. 

Understanding Tax Tech Fatigue

Before diving into solutions, recognize that 73% of change-affected employees face moderate to high stress levels. Tax departments experience this fatigue differently from other business units due to several unique factors: 

• Regulatory pressure creates resistance to innovation. When your team is constantly adapting to new compliance requirements, additional system changes can feel overwhelming rather than helpful. 
• Legacy systems create fragmentation. Tax teams often inherit disconnected tools that don’t communicate effectively, making new technology feel like another band-aid solution rather than a comprehensive fix. 
• High turnover erodes institutional knowledge. When experienced team members leave, the remaining staff may lack context for why changes are necessary or how to implement them effectively. 
• IT-driven projects sideline tax expertise. Technology implementations led primarily by IT departments often miss critical tax-specific requirements and workflows. 

Watch for warning signs of tech fatigue in your organization: growing resistance to new tools, decreased engagement in training sessions, increased turnover or quiet quitting, and growing cynicism toward technological transformation initiatives. 

Pitfall 1: Ignoring Team Readiness and Burnout

Many tax leaders rush into technology implementations without honestly assessing their team’s capacity for change. This oversight can doom even the best-planned projects. 

The mistake:

Launching new systems during peak compliance periods or when your team is already stretched thin handling other initiatives.

The solution:

Start with an honest assessment of team morale and readiness. Use short surveys or one-on-one conversations to uncover underlying resistance before it derails your project.

Download this Change Readiness Assessment to gauge your team’s emotional and practical readiness. 

Consider these practical steps:

• Schedule implementations around your compliance calendar, avoiding busy seasons. 
• Reallocate work or bring in temporary support to create space for learning. 
• Delay non-critical tasks that might compete for attention during the transition. 
• Be transparent about workload concerns and stress levels. 

As one tax leader notes, “There’s never going to be a perfect time, but there are definitely better times. Plan around your team’s reality, not an ideal scenario.” 

Pitfall 2: Leading with Technology Instead of Purpose 

Technical specifications and feature lists don’t motivate people, understanding the “why” behind the change does. When you lead with the “what” instead of the “why,” you miss the opportunity to create genuine buy-in. 

The mistake:

Focusing communication on system capabilities rather than how the technology will improve daily work experience and career satisfaction.

The solution:

Start every conversation with purpose. Explain not just what’s changing, but why it matters for individual team members and the organization’s long-term success.

Effective messaging addresses “What’s in it for me?” questions directly: 

• How will this technology reduce manual work and repetitive tasks? 
• What new skills will team members develop? 
• How does this change position the team for future growth? 
• What compliance risks does this help mitigate? 

Remember that 98% of employees prefer to hear about changes from their direct manager rather than from HR or senior leadership. Ensure your frontline managers understand and can articulate the purpose behind technological changes.

Pitfall 3: Inadequate Stakeholder Engagement

Deloitte’s Touche Tohmatsu CIO Survey identifies resistance to change and inadequate internal sponsorship as the top two barriers to successful ERP implementation. Yet many organizations treat stakeholder engagement as a checkbox rather than a strategic priority. 

The mistake:

Making technology decisions in isolation, then expecting enthusiastic adoption when the solution is already selected and configured.

The solution:

Involve your tax team in conversations before solutions are selected. Their input shapes both the technology choice and the implementation approach.

Create multiple touchpoints for engagement:

• Include tax professionals in vendor demonstrations and selection processes 
• Establish feedback loops through surveys, check-ins, and informal conversations 
• Identify internal advocates who can champion the change peer-to-peer 
• Address individual concerns directly rather than relying only on group communications

Treat buy-in like internal marketing. You’re selling the value to your team, not just implementing software. This requires understanding what motivates each team member and tailoring your approach accordingly. 

Pitfall 4: Poor Communication and Timing Strategies

Effective technology change management requires intentional, multi-channel communication that evolves throughout the implementation process. Many organizations either over-communicate with generic updates or under-communicate, leaving teams confused and anxious.

The mistake:

Using one-size-fits-all communication or waiting until go-live to start serious conversations about change.

The solution:

Develop a structured communication plan that matches messages with appropriate messengers and adjusts tone based on project phases.

Consider this framework for organizing your communication:

• Early Discovery Phase: Include selected team members in solution exploration, using an inclusive tone focused on gathering input. 
• Project Kickoff: Address the entire tax team with inspirational messaging about why the change matters for daily work. 
• Pre-Launch Period: Provide transparent, supportive communication about what’s changing and how to prepare. 
• Go-Live Support: Celebrate the milestone while encouraging the team through initial challenges. 
• Post-Implementation: Maintain reflective, forward-looking dialogue about progress and continuous improvement. 

Mix up your communication formats to maintain engagement. If team meetings feel routine, try informal lunches or breakout discussions to re-energize participation. 

Pitfall 5: Insufficient Post-Implementation Support

Many organizations declare victory at go-live, then wonder why adoption rates remain low or enthusiasm wanes. Sustainable change requires ongoing attention and adjustment. 

The mistake:

Treating implementation as a one-time event rather than an ongoing process that requires continuous refinement.

The solution:

Plan for extensive post-launch support and maintain regular feedback collection to identify issues before they become major blockers.

Effective post-implementation strategies include:

• Frequent check-ins during the first few weeks after go-live. 
• Anonymous feedback channels to surface honest concerns. 
• Regular assessment of whether the technology is delivering intended results. 
• Ongoing training and skill development opportunities. 
• Recognition and celebration of early wins and milestones.

Schedule formal retrospectives to evaluate what worked well and identify areas for improvement for future implementations. Use these insights to refine your technology change management approach for subsequent projects. 

Building Sustainable Technology Adoption

Success with tax technology requires balancing strategic planning with genuine empathy for your team’s experience. The most effective implementations combine structured project management with a people-first mindset that acknowledges the emotional and practical challenges of change.

Transform Your Tax Technology Implementation

Successful tax technology implementations don’t happen by accident. They require deliberate change management strategies that address both technical and human factors. By avoiding these five common pitfalls, you can increase your chances of achieving the efficiency gains, risk reduction, and improved job satisfaction that modern tax technology promises. 

This analysis is intended for informational purposes only and is not tax advice.  For tax advice, consult your tax adviser. See the full disclaimer here.